


For the Hundredth Time

by accol



Category: Supernatural
Genre: Alternate Universe - Gender Changes, Begging, Bondage, M/M, Overstimulation, Sex Toys
Language: English
Status: Completed
Published: 2013-06-20
Updated: 2013-06-19
Packaged: 2017-12-15 13:29:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 1,407
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/850070
Author URL: https://archiveofourown.org/users/accol/pseuds/accol
Summary: <blockquote class="userstuff">
              <p>Gabriel x Sam drabbles originally written for fivesentencesmut.</p>
            </blockquote>





	1. Chapter 1

_Anonymous asked: one proposes marriage_

The one thing that Sam hated about being with Gabe was that he was never 100% sure if Gabe was being serious.  There had been too many examples of Gabriel taking Sam right to the edge of ecstasy and then pulling back over and over until Sam felt like he was going insane; or the time where he stood Sam’s homecooked meal up just to show up three hours later with two girls and a guy for them to share in some kind of dessert apology-joke.  That why Sam blurted out an emphatic and very loud “ _no_ ” when Gabriel asked him to get married.

Proposal after proposal followed:  down on one knee, in the middle of a fuck with Gabriel riding him until he wasn’t sure if he’d heard him right, with flowers, with weapons, with a diamond that Sam suspected was still supposed to be in the Queen’s jewelry box.  And Sam always said no, until the time that Gabriel revealed the ring… pierced through the head of his cock.  

“I did it for you, so now _will you marry me_?”


	2. Chapter 2

_Anonymous asked: Gabriel isn’t the only one who likes to tease._

“You are an evil fucker,” Gabriel said, squirming against the handcuffs that held him face down and spread-eagle on the bed. “Fine, gimme your best shot, Winchester.”

And Sam did… in spades. He started small, just a slicked finger across the rim of Gabe’s hole until Gabe started rocking his hips for a little friction and pushing back to get a little depth, but Sam pulled away to stroke himself about an inch from Gabe’s eager, petulant mouth. Then Sam rubbed the head of his cock over Gabe’s entrance giving him a little of the pressure he wanted, just the crown pushing inside, stretching him for a meager second before Sam pulled away to rub the taste of his precome across Gabe’s lips, drawing back before Gabe could get a mouthful. 

When the first spank landed, Gabriel cried out and rutted against the sheets frantically, forcing his legs wider and ordering Sam to fuck him _now_ ; but Sam just smiled and started the whole sequence over again with a single fingertip.


	3. Chapter 3

_Anonymous asked: using a vibrator on gabe_

Gabe trembled and laughed under Sam’s bodyweight, squirming as he tried to get away from the vibrating tip of the toy. But Sam was holding him fast to the bed, the last of the demon blood making him strong enough and cruel enough to do this, easing the vibrator into Gabriel’s hole and then circling his balls in a tickling torture. 

“I’m not,” Gabriel panted, “going to beg you. I can keep this up forever.”

Sam tightened his grip and plunged it deep, forcing it hard against Gabriel’s prostate and cranking up the rpm until Gabriel thrashed beneath him. Incoherent moans and bitten off words that sounded too close to pleading to be denied accompanied the spasming of Gabriel’s cock as his orgasm was milked from him.


	4. Chapter 4

_Anonymous asked: Supernatural, Sam/Gabriel, Gabriel likes to ride Sam while he’s tied up_

It wasn’t fair really, and Gabriel knew it.  He just really, really _liked_ to see Sam’s huge body spread wide, wrists and ankles wrapped in chains and cock hard with anticipation for Gabe’s next move.  Of course, he would never give Sam what he wanted until he begged for it, letting his ass brush the length of Sam’s dick over and over, hand cupped to his ear as he dramatically listened for those three little words.

“Fuck me, please!” Sam finally bellowed, muscles flexing hard as he tried to rip the chains from the wall.

But maybe Gabriel could make him wait a little longer… maybe Sam would like to watch him with this dildo, fucking himself right above Sam’s cock, using this toy instead of Sam; maybe then Sam would _really_ beg.


	5. Chapter 5

_Anonymous asked: bottom!Sam, sweet dirty talk from Gabe (like dirty talk, but also “I love you” and “You’re so gorgeous” etc)_

Sam stopped mid-lick and looked up at Gabe with his mouth in a flat line.  Being called “pretty” this many times was harshing his ability to give this blowjob because he couldn’t tell if it was the Trickster rearing his head; but Gabe’s face was soft, and his fingers were gentle as they stroked through Sam’s hair, urging Sam onward with murmured praise.  Sam blushed at the attention, not really believing the affection in Gabe’s voice; he was just doing what he could, trying his best like he always did.

Gabriel seemed to read Sam’s mind, curling his hand around Sam’s chin and turning his face upward again before he whispered, “You don’t know half of what I feel for you.”

It was easier when Gabe just fucked him hard and feral; Sam didn’t have to think about his significant others’ track record with early ends…


	6. Chapter 6

_Anonymous asked: “Enough orgasms to last you a lifetime, all in one night” (fully consensual, please)_

“Remember that little video message I made for you?   _Casa Erotica_ ,” Gabriel said the title that had burned itself firmly into Sam’s brain with a little extra oomph.  “Tell me, Sam, how many times did you watch it?  Don’t lie to old Gabe.”

Sam looked away and Gabriel pulled him back with a single finger.  “Fine.  Let’s just say more than once,” Sam admitted, knowing full well that he could identify every last hair on Gabriel’s body from the number of times he had jerked off to the sight of Gabriel fucking into that woman, inexplicably wishing that it was him on that bed instead of her.

Gabriel’s smile broadened as his hand reached down to cup Sam through his jeans, fingers massaging behind his balls with obvious intent.  “What do you say we make a sequel?   _Casa Erotica: The “it’s only Wednesday when Sam is milked dry” edition_ ,” he said, and Sam already felt his first orgasm building in his balls and cock, propelled forward by the thought of having this movie whenever he wanted it, forever watching himself orgasm over and over at Gabriel’s touch. ****


	7. Chapter 7

_Anonymous asked: Fem!Sam/Gabe, He can keep going and going and going, all night long- overstimulation of Sam_

Her long hair was soaked with sweat and a lock of it clung to her flushed cheek; the sheets beneath her arching body were damp, but she refused to beg him to stop.  All she had to do was figure out how to turn the tables and take Gabe down, make him be the one incoherent with pleasure, and then he couldn’t lord this over her with that aggravating smirk on his face.

But he wasn’t making it easy to focus her thoughts around what would make him go insane with lust.  For the hundredth time his lips were closing around her clit, his tongue was tickling her entrance, and his fingers… they fluttered like feathers over her skin.  She screamed with another release — she lost count by now — and then groaned as he slid into her wetness and began again.


	8. Chapter 8

_Anonymous asked: Sam/Gabriel/Castiel, Castiel is depressed because Dean won’t admit his feelings, so Sam and Gabe invite him to join them._

He watched the tail lights of Dean’s car disappear down the long road outside the motel and thought about chasing him, flying to his car and forcing him to pull over; but there was no way he could take from Dean what he wanted, because that was a thing that had to be given willingly.

Gabriel fluttered into the space next to Castiel, looking across the empty expanse of dark and wet pavement before bumping his shoulder into his friend’s and inclining his head back toward their room.  

“C’mon,” Gabriel said simply, not saying out loud that he and Sam could help him forget for a few moments, that maybe he should keep on forgetting after his skin had cooled.

But it didn’t work that way.  Castiel couldn’t forget the soft and then laughing and then ferocious look in Dean’s hazel eyes when the same look was gazing up at Gabriel from Sam, and he couldn’t let the thought of Dean arching beneath him be, not when he gripped Sam’s shoulder and felt as though he’d been burned with the first, painfully beautiful sight of Dean in the pit.  They helped him come to a release, but they could never be Dean Winchester.


End file.
